Winthrop has 2 hiking trails. These trails range from 0 to 3 miles in length. The most popular trail is Boston Harbor: Spectacle Island. Trails.com member Courtney D. recently completed Boston Harbor: Spectacle Island. See all Winthrop trails.
Boston Harbor: Spectacle Island
Once a landfill, Spectacle Island offers amazing views of Boston and the coast from the highest point in Boston Harbor.
This entire hike is historic, since you travel trails designed by world-famous landscape architect Frederick Law Olmsted. ...